ZC-B

ZC-B

Identifiers
IUPAC name 3-(4-bromo-2,5-dimethoxyphenyl)azetidine
CAS Number	2641630-65-9
PubChem CID	156337249
UNII	9EP4MV3URL
Chemical and physical data
Formula	C11H14BrNO2
Molar mass	272.142 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=CC(=C(C=C1C2CNC2)OC)Br
InChI InChI=1S/C11H14BrNO2/c1-14-10-4-9(12)11(15-2)3-8(10)7-5-13-6-7/h3-4,7,13H,5-6H2,1-2H3 Key:YFCASESLVDHSAW-UHFFFAOYSA-N

ZC-B (3-(4-bromo-2,5-dimethoxyphenyl)azetidine) is a phenethylamine derivative which acts as a serotonin receptor agonist selective for the 5-HT₂ subtypes, with an EC₅₀ of 1.6nM at 5-HT_2A, vs 5.8nM at 5-HT_2C. It is structurally related to the psychedelic phenethylamines 2C-B and DOB, but with the amine side chain conformationally restricted as an azetidine ring. ^{[1] [2] [3]}

See also

• Cyclized phenethylamine
• DOB
• β-Methyl-2C-B
• 2C-B-PYR
• 4C-B
• TCB-2
• LPH-5
• LSZ

References

1. US 2021/0137908,Kristensen JL, Jensen AA, Märcher-Rørsted E,"5-HT2A Agonists for Use in Treatment of Depression.",published 13 May 2021, assigned to Lophora ApS. 
2. WO 2022/221774,Johnson G, Nichols DE, Maillet EL,"Aryl-ring-substituted 3-phenylazetidines and their use in methods for treating 5-HT2 responsive conditions",published 2022-10-20, assigned to leusis Therapeutics US Inc. 
3. Sabnis RW (September 2025). "Novel Compounds as 5‑HT2A Agonists for Treating Depression". ACS Medicinal Chemistry Letters. 16 (9): 1709–1710. doi:10.1021/acsmedchemlett.5c00461. PMID   40959260.